Weekend Winter Getaways near Chicago, IL

Although Chicago is known as the “Windy City,” you won’t have to worry about chilly winds ruining your weekend experience. In fact, the term simply refers to the city’s politicians. If cozying up in front of fireplaces while sipping hot cocoa or wine is your thing, check out Allium, where rustic charm merges with high living for the perfect place to cuddle up. Chicago is home to a number of art venues and museums you can enjoy, including Broadway in Chicago, Steppenwolf Theatre Company, the Museum of Science and Industry, and Adler Planetarium. The latter hosts evening events, juxtaposing exhibit viewing with cocktails. You’re probably wondering where you’re staying at this point, so check out this unique assortment of listings below. You’ll find everything from tree houses to reimagined caravans. It’s easy; just pick one.